Jimmy Kimmel and Sarah Silverman's Relationship Timeline

They laughed, they sparred, and they stumbled through seven years of love that felt more like a sitcom than a fairytale. For the TV host and the actress, romance was never tidy — it was messy, sharp-edged, and strangely tender, a relationship that blurred the line between punchline and partnership.

It all started with a cruel roast joke — but ended in two breakups, bittersweet memories, and a friendship that somehow survived it all. Jimmy Kimmel and Sarah Silverman may have spent seven years together, but it was a brutal punchline at Hugh Hefner's Comedy Central roast that lit the fuse on one of comedy's most talked-about romances.

Silverman recalled that their first encounter wasn't at the Playboy Mansion, but during the Comedy Central roast, where Kimmel was serving as host. At the time, she barely knew him, and the format required them to trade sharp, mean-spirited jokes with one another.

Her voice tinged with that mix of sarcasm and affection, she said, "It's funny because I found my three-by-five card that I scribbled my joke about him on, and I found it, and he has it on his wall, but looking back on it [... ] I say, 'Jimmy Kimmel, everybody, uh he's fat and has no Charisma, watch your back Danny Aiello.'"

But behind the barbs, a spark quietly smoldered — one that wouldn't catch fire until much later.

Comedy, Crank Calls, and a Kiss 40 Minutes in the Making

The slow-burn connection simmered long after the roast was over. Silverman revealed that it wasn't until Kimmel brought her into his world professionally that the two started spending real time together.

"No, actually, it was a long time after that that we started dating. He hired me on his Crank Yankers show to make crank calls, and about the second season, we started hanging out and watching movies together," she said.

Their friendship soon tipped into something more, and in classic awkward-comedy fashion, their first kiss was anything but effortless, as Silverman remembered:

"One night we were watching Broadway Danny Rose. Jimmy went in for the first kiss, and both of us -- we were probably nose to nose for what seemed like forty minutes before either of us had the guts to just go ahead and kiss. But once we did, we started making out like crazy. It had been festering for a very long time."

Kimmel and Silverman's private life carried the same quirky edge as their comedy, where vulnerability often doubled as a setup for laughter. Even their most personal confessions became punchlines, shaping a relationship defined by blunt honesty and irreverent humor.

The actress also teased, "He doesn't like anyone to think I'm attractive. It makes him crazy." Kimmel matched her beat for beat, "Sarah claims that she never moves her bowels."

The couple became a real-life sitcom, full of quirky moments and offbeat tenderness, always punctuated by their signature wit. Kimmel once joked, "We have a unique relationship in that I'm the woman and Sarah's the man."

Silverman fired right back, "First of all, I'm very impressed that you've learned that men and women are different. I think that's incredibly original, and I'm blown away by your mind." Their bond thrived on that razor-thin line between affection and insult, honesty and hilarity.

Breakups, Bonding, and the Battle with Inner Demons

Even as their love unraveled — not once, but twice — their connection proved challenging to sever. After five years together, they called it quits, with representatives confirming the end through a single, corporate-sounding line. "Jimmy and Sarah have and will have no further comment," the pair's representatives said.

But reconciliation came quickly. And just as fast, a second heartbreak followed when a source confirmed to People that after briefly rekindling their romance, Kimmel and Silverman ultimately ended their relationship once again.

Still, even after romance faded, a deep emotional tie lingered. Kimmel said, "Sarah [Silverman] and I, we're like brothers," adding that he never understood the idea of cutting someone out after years together.

At Silverman's Hollywood Walk of Fame ceremony, Kimmel showed his humor was as sharp as ever, playfully noting that in her lengthy autobiography, she wrote about him only a handful of times but devoted far more space to her trademark fart jokes — a reminder of what he called her true first love.

Their story was never perfect—but it was undeniably real. From late-night Scrabble sessions to sharing games with his kids, their time together was filled with a strange and tender intimacy.

"When we have a night alone, like a Saturday night with no kids, we'll go to this restaurant we really like and sit at the bar and play Scrabble on our phones. We have two games going, so we can go back and forth. There's constant action," Silverman disclosed during an interview with Slate.

The actress also formed a close bond with Kimmel's children, often joining in on family games. One of her favorites was 20 Questions, a pastime she loved for its ability to bring everyone together across ages, primarily when the answers centered on familiar people from their lives or popular culture.

But behind all the laughs, darker battles brewed quietly for Silverman. In a strikingly candid moment, she opened up about her mental health journey.

"Yes. Yeah! I never went off it. I really lucked out because I see people always trying a million different antidepressants. Whatever chemical imbalance I have, Zoloft fit perfectly because I take a half-pill every night before I go to bed. I don't feel like I don't have highs or lows, but what's missing is that complete downward spiral into despair about nothing [sic]," she disclosed.

She explained that her struggle with the condition first began in her early teens, eased for a while, but returned with full force in her early twenties. With guidance from her mother and an aunt who was a psychologist, she sought help.

Later, when she wondered about managing without medication, her psychiatrist reminded her that treatment was just as essential as it would be for any chronic illness like diabetes.

While Silverman has continued to speak openly about her personal demons, Kimmel has faced a different kind of pressure — this time under the blinding lights of his late-night talk show, as controversy brewed once again.

Kimmel Seen Looking Downcast in LA

On a warm Thursday afternoon, September 18, 2025, in Los Angeles, the late-night host made a public appearance, just one day after ABC abruptly pulled the plug on his show "Jimmy Kimmel Live!"

What appeared to be a stop at his attorney's office quickly spiraled into a full-blown online firestorm, as photos of Kimmel emerged showing what the internet believed to be a defeated man behind the wheel of his car.

Clad in a crisp navy button-down and black slacks, Jimmy Kimmel, 57, was seen stepping out of a sleek black Audi — but the swagger, online viewers believe, was gone. Clutching a notepad, car keys, and a wallet, and wearing dark sunglasses, the host gave a brief smile to waiting photographers. Still, his demeanor did not go unnoticed by online spectators.

Kimmel's outing quickly sparked debate online, with spectators dissecting everything from his facial expression to his overall demeanor. Some were convinced there was more beneath the surface.

"Looks like he's been crying 🙁," remarked one commenter, while another suggested, "He's smiling, but he's crying inside." Echoing that sentiment, someone else added, "Hiding the tears." Others noted a perceived change in his appearance, with one person stating, "Doesn't look like Jimmy Kimmel."

Photos Emerge After ABC Axes His Show

The public sighting followed confirmation made on Wednesday, September 17, from Disney's ABC that it would be suspending "Jimmy Kimmel Live!" from its schedule indefinitely.

The sudden move followed a bombshell announcement from Nexstar Media Group, which refused to air Kimmel's show across more than 200 television stations it controls in 116 markets.

For all the laughter they shared and the heartbreaks they weathered, Kimmel and Silverman's story remains a reminder that even comedians live through moments no punchline can soften.

As both continue to face new battles under very different spotlights, their history stands as a reminder that some relationships don't end; they change shape, carrying the warmth of what once was into whatever comes next.